AU2004212039A1 - Novel crystalline modification of the anhydrate of boscalid - Google Patents
Novel crystalline modification of the anhydrate of boscalid Download PDFInfo
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- AU2004212039A1 AU2004212039A1 AU2004212039A AU2004212039A AU2004212039A1 AU 2004212039 A1 AU2004212039 A1 AU 2004212039A1 AU 2004212039 A AU2004212039 A AU 2004212039A AU 2004212039 A AU2004212039 A AU 2004212039A AU 2004212039 A1 AU2004212039 A1 AU 2004212039A1
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- anhydrate
- modification
- preparation
- Prior art date
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- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 title claims description 24
- 238000012986 modification Methods 0.000 title description 34
- 230000004048 modification Effects 0.000 title description 34
- 239000005740 Boscalid Substances 0.000 title description 20
- 229940118790 boscalid Drugs 0.000 title description 20
- 150000001875 compounds Chemical class 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims 3
- 239000004009 herbicide Substances 0.000 claims 3
- 239000003586 protic polar solvent Substances 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- 241000233866 Fungi Species 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004562 water dispersible granule Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004548 suspo-emulsion Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005337 ground glass Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Centrifugal Separators (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
IN THE MATTER OF an Australian Application corresponding to PCT Application PCT/EP2004/000703 RWS Group Ltd, of Europa House, Marsham Way, Gerrards Cross, Buckinghamshire, England, hereby solemnly and sincerely declares that, to the best of its knowledge and belief, the following document, prepared by one of its translators competent in the art and conversant with the English and German languages, is a true and correct translation of the PCT Application filed under No. PCT/EP2004/000703. Date: 17 May 2005 C. E. SITCH Deputy Managing Director - UK Translation Division For and on behalf of RWS Group Ltd Novel crystalline modification of the anhydrate of boscalid The present invention relates to monoclinic 2-chloro-N-(4'-chlorobiphenyl-2 yl)-nicotinamide melting at 147 - 148 0 C and of the formula 1 5 0 '- N N CI CI The present invention furthermore relates to the preparation thereof: Monoclinic 2-chloro-N-(4'-chlorobiphenyl-2-yl)nicotinamide melting at 144 - 145 0 C and 10 of the formula I is described in EP-A-545 099 and PCT/EP02/10320 and is known under the common name boscalid. PCT/EPO2/10320 describes the anhydrate and the hydrate of boscalid and also the preparation of boscalid hydrate from boscalid anhydrate. 15 The known anhydrate of boscalid is referred to in this Application as modification I and the anhydrate of boscalid as claimed in claim 1 is referred to as modification 11. In order to prepare an aqueous suspension concentrate (SC) or a suspoemulsion (SE) from the anhydrate of boscalid, according to PCT/EP02/10320 it is first necessary to 20 prepare the hydrate of boscalid, which is then very finely milled in the presence of water and further assistants. This is not possible with the anhydrate of boscalid since, when this is milled with the assistants in water, it forms a loamy solid which hinders the further milling process. 25 According to PCT/EPO2/10320, the hydrate of boscalid of modification I is prepared by dissolving the anhydrate of boscalid of modification I in a water-soluble solvent and then precipitating the hydrate by adding water. Solid formulations, such as spray-dried or extruded water-dispersible granules, can be 30 prepared directly from the anhydrate of boscalid of modification I without having to carry out a conversion to the hydrate beforehand. If these water-dispersible granules are then diluted with water and are mixed with solvent-containing crop protection preparations, for example emulsion concentrates 35 (EC), problems may arise during application since boscalid crystals form and may then block the filters in application apparatuses.
2 It is an object of the present invention to eliminate the deficiencies described in the case of the water-dispersible granules. We have found that this object is achieved by providing the monoclinic anhydrate of 5 boscalid of the formula I of modification 11 which melts at 147 -148 0 C. Surprisingly, it was found that the anhydrate of boscalid of the formula I in the form of modification 11 shows scarcely any crystal growth in the presence of solvents. The preparation of the anhydrate of boscalid of formula I of modification I is described 10 in EP-A-545 099 and PCT/EP02/10320. The present invention furthermore relates to processes for the preparation of anhydrate of boscalid of modification 11. 15 In one embodiment (process 1), the process comprises the following steps: a) dissolution of the anhydrate of the compound of the formula I of modification I in a polar organic solvent or an aromatic hydrocarbon, 20 b) precipitation of the anhydrate of the compound of the formula I of modification Il by cooling the solvent. Suitable polar solvents are alcohols, glycols, ketones, ethers, esters, amides and mixtures of these solvents. Aromatic hydrocarbons are furthermore suitable. 25 Examples of alcohols are methanol, ethanol and propanol. Methanol is particularly preferred. Suitable glycols are, for example, ethylene glycol and diethylene glycol. 30 Suitable ketones are, for example, acetone and cyclohexanone. Suitable ethers are, for example, dioxane and tetrahydrofuran. 35 A suitable ester is, for example, ethyl acetate. A suitable amide is, for example, dimethylformamide. Suitable aromatic solvents are, for example, benzene, toluene and xylene. 40 3 The dissolution of the anhydrate of the compound of the formula I of modification I in stage a) is effected at from 20 to 1500C, preferably from 40 to 1150C, particularly preferably from 50 to 95*C. 5 The precipitation of the anhydrate of the compound of the formula I of modification Il in stage b) is effected by cooling the solution obtained in stage a) to temperatures of from 0 to 300C, preferably from 10 to 250C, particularly preferably from 20 to 250C. The precipitation is effected over a period of from 1 to 24, preferably from 2 to 20, hours. 10 The addition of seed crystals of the anhydrate of the compound of the formula I of modification 11 in stage b) is particularly advantageous, substantially accelerating the precipitation. In a further embodiment (process 2), the process comprises the following steps: 15 a) heating of the anhydrate of the compound of the formula I of modification I to above 1500C until everything has melted, b) cooling of the melt with addition of seed crystals of the anhydrate of the 20 compound of the formula I of modification Hl. The seed crystals are added in stage b) in an amount of from 0.01 to 20, preferably from 0.5 to 5, % by weight. 25 This process is preferably carried out in a suitable stainless steel vessel. The conversion of the anhydrate of the compound of the formula I of modification I into modification 11 takes place quantitatively. The physical properties of the two modifications of the anhydrates of the compound of 30 the formula I are compared in table 1: 4 Table 1 Properties Anhydrate, modification I Anhydrate, modification Il Molecular weight 342 342 [g/mol] Melting point [*C] (DSC) 144.8 147.2 Heat of fusion [J/g] (DSC) 85 106 Density [g/cm 3 ] 1.399 1.457 Characteristic IR bands 924, 1310, 1650 868, 917, 1675 [cml] 5 The cell parameters from the crystallographic investigations using a single crystal diffractometer from Siemens are shown in table 2: Table 2 10 Parameter Anhydrate, modification I Anhydrate, modification || Class Monoclinic Monoclinic Space group P21/c P21/c a 1479.2(3) pm 1162.5(6) pm b 1157.67(19) pm 1134.2(4) pm c 1872.1(3) pm 1283.2(5) pm a 90* 9 0 * P 91.993 (17)* 114.52(4)* y 900 90* Volume 3.2038(9) nm 3 1.5390 nm 3 Z 8 4 Density (calculated) 1.423 mg/m 3 1.481 mg/m 3 R', wR 2 0.1036; 0.1699 0.0489; 0.1264 The parameters shown have the following meaning: a,b,c = edge lengths of the unit cell 15 a,p,y = corresponding angles Z = number of molecules in the unit cell 5 Example 1: Preparation of the anhydrate of the compound of the formula I of modification 11: 5 30 g of methanol are initially taken in a conical flask having a ground glass joint. Thereafter, 5 g of anhydrate of the compound of the formula I of modification I are added and the mixture is heated to 550C in a water bath while stirring until everything has dissolved (about 10 minutes). Thereafter, the flask is removed from the heating bath and then left to cool for a period of 18 hours at ambient temperature (about 200C). 10 Anhydrate of the compound of the formula I of modification 11 crystallizes out. Melting point 147.2*C Example 2: 15 200 g of anhydrate of the compound of the formula I of modification I are heated to 1600C in a stainless steel vessel. The melt is then cooled while stirring. At 150"C, seeding is effected with crystals of the anhydrate of the compound of the formula I of modification 11 and cooling is continued. Anhydrate of the compound of the formula I of 20 modification 11 is obtained. Example 3: 25 Preparation of water-dispersible granules of anhydrate of the compound of the formula I of modification I or II: Composition: 30 Component Concentration Boscalid (active ingredient) 30 - 60% w/w Dispersant (ligninsulfonate salt) 10 - 20% w/w Wetting agent (naphthalenesulfonic acid 5 - 10% w/w condensate salt) Antifoam (silicone oil) 0.5 - 1% w/w Standardizing agent (sodium sulfate) to 100% 6 Preparation process: A suspension of suitable concentration is prepared and is milled to the desired particle size (50% < 2 pm) by means of a pearl mill. The suspension is then dried in a spray 5 tower. Comparison of the tank mixing compatibility: For this purpose, both water-dispersible granules of the above composition, comprising anhydrate of the compound of the formula I of modification I (formulation A), and water 10 dispersible granules of anhydrate of the compound of the formula I of modification II (formation B) were prepared. A 5% strength suspension of the respective water-dispersible granules in CIPAC D water (Ca**/Mg** (4:1) hardness of 342 ppm and pH of from 6.0 to 7.0) was then 15 prepared. This suspension was then mixed with 1% of Solvesso 200 (mixture of aromatic hydrocarbons) as a typical solvent for solvent-containing liquid formulations (e.g. EC). The corresponding spray liquor was then stored over a certain period at a certain temperature. For assessing the quality, the solid residue on a 75 pm sieve was determined after the storage. 20 Result Formulation Storage time Storage Residue on temperature 75 pm sieve A 24 hours 20 0 C 13.0 % w/w A 24 hours 30 0 C 14.3 % w/w A 7 days 20 0 C 16.8 % w/w A 7 days 30 0 C 19.3 % w/w B 24 hours 20 0 C 0.1% w/w B 24 hours 40 0 C Traces B 7 days 20 0 C Traces B 7 days 40 0 C 0.1% w/w
Claims (10)
1. Monoclinic 2-chloro-N-(4'-chlorobiphenyl-2-yl)nicotinamide melting at 147 - 148*C and of the formula 1 5 N N N N Cl Cl
2. A process for the preparation of the compound I as claimed in claim 1, wherein a) 2-chloro-N-(4'-chlorobiphenyl-2-yl)nicotinamide melting at 144 - 145*C and 10 of the formula I is dissolved in a protic polar solvent or an aromatic hydrocarbon and b) crystallizes out of the solvent after cooling.
3. A process for the preparation of the compound I as claimed in claim 2, wherein 15 the protic polar solvent used is an alcohol, glycol, ketone, ether, ester or amide or dimethyl sulfoxide or a mixture thereof.
4. A process for the preparation of the compound I as claimed in claim 3, wherein the protic polar solvent used is an alcohol, ester or ketone. 20
5. A process for the preparation of the compound I as claimed in claim 4, wherein the alcohol used is methanol or ethanol.
6. A process for the preparation of the compound I as claimed in claim 2, wherein 25 the compound of the formula I is dissolved at from 20 to 150*C in stage a).
7. A process for the preparation of the compound I as claimed in claim 2, wherein the compound of the formula I is dissolved at from 40 to 1150C in stage a). 30
8. A herbicide comprising the compound of the formula I as claimed in claim 1 and inert additives.
9. A herbicide as claimed in claim 8, which comprises from 0.1 to 95% by weight of the compound of the formula I as claimed in claim 1. 8
10. A method for controlling harmful fungi, wherein the harmful fungi, their habitat or the plants, area, materials or spaces to be kept free from them are treated with a fungicidal amount of a compound of the formula I as claimed in claim 1 or a herbicide as claimed in claim 7 and comprising the compound of the formula I as 5 claimed in claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10307751A DE10307751A1 (en) | 2003-02-14 | 2003-02-14 | New monoclinic boscalide crystal modification with defined melting point useful as herbicide |
| DE10307751.0 | 2003-02-14 | ||
| PCT/EP2004/000703 WO2004072039A1 (en) | 2003-02-14 | 2004-01-28 | Novel crystalline modification of the anhydrate of boscalid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004212039A1 true AU2004212039A1 (en) | 2004-08-26 |
| AU2004212039B2 AU2004212039B2 (en) | 2010-07-22 |
Family
ID=32748027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004212039A Expired AU2004212039B2 (en) | 2003-02-14 | 2004-01-28 | Novel crystalline modification of the anhydrate of boscalid |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7501384B2 (en) |
| EP (1) | EP1597232B1 (en) |
| JP (1) | JP4642743B2 (en) |
| KR (2) | KR101146432B1 (en) |
| CN (1) | CN100494179C (en) |
| AP (1) | AP1955A (en) |
| AR (2) | AR043175A1 (en) |
| AT (1) | ATE339405T1 (en) |
| AU (1) | AU2004212039B2 (en) |
| BR (1) | BRPI0407358B1 (en) |
| CA (1) | CA2515725C (en) |
| CL (1) | CL2004000256A1 (en) |
| CR (1) | CR7939A (en) |
| CY (1) | CY1107513T1 (en) |
| DE (2) | DE10307751A1 (en) |
| DK (1) | DK1597232T3 (en) |
| EA (1) | EA008004B1 (en) |
| EC (1) | ECSP055948A (en) |
| ES (1) | ES2273211T3 (en) |
| HR (1) | HRP20050803B1 (en) |
| MA (1) | MA27619A1 (en) |
| ME (1) | ME00061B (en) |
| MX (1) | MXPA05007962A (en) |
| NO (1) | NO329988B1 (en) |
| NZ (1) | NZ542308A (en) |
| OA (1) | OA13150A (en) |
| PL (1) | PL219123B1 (en) |
| PT (1) | PT1597232E (en) |
| RS (1) | RS51685B (en) |
| SI (1) | SI1597232T1 (en) |
| UA (1) | UA81659C2 (en) |
| WO (1) | WO2004072039A1 (en) |
| ZA (1) | ZA200507344B (en) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA90035C2 (en) | 2005-11-10 | 2010-03-25 | Басф Се | Fungicidal mixture comprising boscalid and pyrimethanil and method for control of phytopathogenic fungi |
| BRPI0815085A2 (en) * | 2007-08-09 | 2014-09-30 | Basf Se | FUNGICIDE MIXTURES, FUNGICIDE AGENT, PROCESS TO COMBAT PHYTOPATHOGENIC HARMFUL FUNGES, SEED, AND USE OF COMPOUNDS. |
| JP2013510113A (en) | 2009-11-06 | 2013-03-21 | ビーエーエスエフ ソシエタス・ヨーロピア | Crystalline complex of 4-hydroxybenzoic acid and selected pesticide |
| WO2012031355A1 (en) | 2010-09-09 | 2012-03-15 | Suncor Energy Inc. | Synergistic paraffinic oil and boscalid fungicides |
| CN102217604B (en) * | 2011-04-16 | 2013-11-06 | 陕西汤普森生物科技有限公司 | Bactericidal composition containing boscalid and triazole compounds |
| CN102860307B (en) * | 2012-09-13 | 2014-04-02 | 倪烈 | Compound pesticide containing validamycin and cyprosulfamide and application of compound pesticide |
| CN103348982B (en) | 2013-07-15 | 2016-06-15 | 江苏龙灯化学有限公司 | A kind of Fungicidal mixture |
| CN103980192B (en) * | 2014-01-20 | 2016-02-17 | 泰州百力化学股份有限公司 | A kind of method of selectivity synthesis different crystal forms boscalid amine |
| CN104016915B (en) * | 2014-06-27 | 2016-03-30 | 重庆工商大学 | A kind of preparation method of boscalid |
| CN104920366A (en) * | 2015-05-14 | 2015-09-23 | 京博农化科技股份有限公司 | Processing method of boscalid preparation |
| GB2539022B (en) * | 2015-06-04 | 2018-02-07 | Rotam Agrochem Int Co Ltd | Process for preparing boscalid |
| GB2536979B (en) * | 2015-06-04 | 2019-03-13 | Rotam Agrochem Int Co Ltd | Process for preparing boscalid |
| GB2550138B (en) * | 2016-05-09 | 2019-06-12 | Rotam Agrochem Int Co Ltd | Process for preparing boscalid |
| GB2552694B (en) * | 2016-08-04 | 2020-03-04 | Rotam Agrochem Int Co Ltd | A Synergistic fungicidal composition and use thereof |
| GB2552697B (en) * | 2016-08-04 | 2021-03-10 | Rotam Agrochem Int Co Ltd | Process for the preparation of boscalid |
| GB2552696B (en) * | 2016-08-04 | 2020-03-04 | Rotam Agrochem Int Co Ltd | Process for preparing boscalid |
| GB2552699B (en) * | 2016-08-04 | 2021-03-10 | Rotam Agrochem Int Co Ltd | Process for preparing boscalid |
| GB2552695B (en) * | 2016-08-04 | 2020-03-04 | Rotam Agrochem Int Co Ltd | A synergistic fungicidal composition |
| WO2018060836A1 (en) | 2016-09-28 | 2018-04-05 | Upl Limited | Process for preparation of boscalid anhydrate form i and boscalid anhydrate form ii |
| CN115536581A (en) * | 2022-10-08 | 2022-12-30 | 河北兰升生物科技有限公司 | Preparation method of high-purity boscalid crystal form I |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH657129A5 (en) | 1983-12-20 | 1986-08-15 | Sandoz Ag | Process for preparing N-thienylchloroacetamides |
| CA2081935C (en) | 1991-11-22 | 2004-05-25 | Karl Eicken | Anilide derivatives and their use for combating botrytis |
| TW431861B (en) * | 1997-12-18 | 2001-05-01 | Basf Ag | Fungicidal mixtures based on amide compounds and azoles |
| DK1432685T3 (en) * | 2001-09-25 | 2005-05-30 | Basf Ag | Crystalline hydrates of anilide derivatives such as fungicides and insecticides |
| NZ535307A (en) * | 2002-03-21 | 2007-09-28 | Basf Ag | Fungicidal mixtures comprising prothioconazole and boscalid |
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